Conventionally, as a method of producing a pyridine derivative having a substituent at the 2-position of a heterocyclic structure, (1) a method comprising reacting an organometallic compound having a heterocyclic structure with a 2-halogenated pyridine derivative in the presence of a transition metal catalyst [Synthesis, vol. 1, p. 128 (2001); Journal of Organic Chemistry, vol. 66, No. 4, p. 1500 (2001); WO01/04076 and the like], (2) a method comprising reacting a 2-pyridyl organometallic compound with a halogenated heterocyclic compound in the presence of a transition metal catalyst [Tetrahedron Letters, vol. 41, No. 10, p. 1653 (2000); WO99/65896; Tetrahedron, vol. 52, No. 15, p. 5625 (1996) and the like], (3) a method comprising reacting 2-pyridylsulfoxide with a Grignard reagent having a heterocyclic structure [Liebigs Annalen/Recueil, vol. 2, p. 297 (1997); Bulletin of the Chemical Society of Japan, vol. 62, p. 3848 (1989) and the like] and the like are known.
The above-mentioned methods (1) and (2) require use of a transition metal catalyst, which is expensive and whose waste liquid has a pollution problem, and the reaction does not proceed without the catalyst. In method (3), selectivity of the reaction is low because a bipyridine derivative due to homocoupling reaction is produced as a byproduct.